Sodium Hydroxide → HCID 57994320, compound

HRID 1009975Notes

Reaction equation

HRID 1009975 reaction equation
C1([O:6][C:7](=[O:33])[C@@H:8]([NH:29][C:30](=[O:32])[CH3:31])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:28])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](=[O:27])[NH:25][OH:26])=[CH:12][CH:11]=2)CCCC1.[OH-].[Na+]>O>[C:30]([NH:29][C@@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:28])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](=[O:27])[NH:25][OH:26])=[CH:12][CH:11]=1)[C:7]([OH:33])=[O:6])(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15952895HCID 15952895, compound

Product 1

HCID 57994320HCID 57994320, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Stage 6 resin loaded with Compound 1 (0.3 g, 1.14 mmol/g) was treated with sodium hydroxide (0.068 g), in water (2 ml, 0.85 M) and the reaction shaken for 4 hrs. The resin was washed, DCM, DMF (×2), DCM, MeOH (×2), MeOH, TBME and dried. The required product was cleaved with 2% TFA/DCM to give crude compound 2, which was further purified by preparative HPLC. m/z 394 [M++H]+, 1H NMR (400 MHz, d4-MeOH) δ: 1.39-1.44 (4H, m, 2×CH2), 1.63-1.71 (4H, m, 2×CH2), 1.90 (3H, s, CH3CO), 2.11 (2H, t, CH2), 2.37 (2 H, t, CH2), 2.92 (1 H, dd, ArCH), 3.17 (1 H, dd, ArCH), 4.65 (1 H, q, NHCH), 7.19 (2 H, 2 d, Ar), 7.48 (2 H, d, Ar).

Workup

  1. washThe resin was washed
  2. dry with materialDCM, DMF (×2), DCM, MeOH (×2), MeOH, TBME and dried

Sources & evidence

ORD record
ord-fbf9b4dff2344b058bdc67424eaf6560
Source dataset
uspto-grants-2011_07
Patent number
US07973181B2

Reaction notes

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